US2010173777A1PendingUtilityA1

Piperazine Compounds Having Herbicidal Action

Assignee: BASF SEPriority: Jun 12, 2007Filed: Jun 11, 2008Published: Jul 8, 2010

Est. expiryJun 12, 2027(~0.9 yrs left)· nominal 20-yr term from priority

Inventors:Eike Hupe Thomas Seitz Matthias Witschel Dschun Song William Karl Moberg Liliana Parra Rapado Frank Stelzer Andrea Vescovi Trevor William Newton Robert Reinhard Bernd Sievernich Klaus Grossmann Thomas Ehrhardt Michael Rack Elmar Kibler

C07D 241/08A01N 43/60

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References

Claims

Abstract

The present invention relates to piperazine compounds of the general formula I defined below and to their use as herbicides. Moreover, the invention relates to compositions for crop protection and to a method for controlling unwanted vegetation. R 1 is selected from the group consisting of halogen, cyano, nitro, Z—C(═O)—R 12 , phenyl and a 5- or 6-membered heterocyclic radical which has 1, 2, 3 or 4 heteroatoms selected from the group consisting of O, N and S as ring atoms, where phenyl and the heterocyclic radical are unsubstituted or may have 1, 2, 3 or 4 substituents R 1a ; Z is a covalent bond or a CH 2 group; R 12 is hydrogen, C 1 -C 6 -alkyl, C 3 -C 6 -cycloalkyl, C 2 -C 6 -alkenyl, C 5 -C 6 -cycloalkenyl, C 2 -C 6 -alkynyl and the like; R 2 is hydrogen, halogen, nitro, cyano, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 2 -C 4 -alkenyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, benzyl or a group S(O) n R 21 in which R 21 is C 1 -C 4 -alkyl or C 1 -C 4 -haloalkyl and n is 0, 1 or 2; R 3 is hydrogen or halogen; R 4 is C 1 -C 4 -alkyl, C 3 -C 4 -alkenyl or C 3 -C 4 -alkynyl; R 5 is hydrogen, C 1 -C 4 -alkyl, C 3 -C 4 -alkenyl, C 3 -C 4 -alkynyl or a group C(═O)R 51 in which R 51 is hydrogen, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy or C 1 -C 4 -haloalkoxy; R 6 is C 1 -C 4 -alkyl, C 1 -C 4 -hydroxyalkyl or C 1 -C 4 -haloalkyl; R 7 , R 8 independently of one another are hydrogen, OH, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkyloxy, C 1 -C 4 -alkyl or C 1 -C 4 -haloalkyl; R 9 , R 10 independently of one another are selected from the group consisting of hydrogen, halogen, CN, NO 2 , C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 2 -C 4 -alkenyl, C 1 -C 4 -alkoxy and C 1 -C 4 -haloalkoxy; and R 11 is hydrogen or C 1 -C 4 -alkyl; and the agriculturally useful salts of these compounds.

Claims

exact text as granted — not AI-modified

1 - 16 . (canceled) 
     
     
         17 . A piperazine compound of the formula I 
       
         
           
           
               
               
           
         
         in which 
         R 1  is selected from the group consisting of halogen, cyano, nitro, Z—C(═O)—R 12 , phenyl and a 5- or 6-membered heterocyclic radical which has 1, 2, 3 or 4 heteroatoms selected from the group consisting of O, N and S as ring atoms, where phenyl and the heterocyclic radical are unsubstituted or may have 1, 2, 3 or 4 substituents R 1a  independently of one another selected from the group consisting of halogen, CN, NO 2 , C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy and C 1 -C 4 -haloalkoxy, and in which 
         Z is a covalent bond or a CH 2  group; 
         R 12  is hydrogen, C 1 -C 6 -alkyl, C 3 -C 6 -cycloalkyl, C 2 -C 6 -alkenyl, C 5 -C 6 -cycloalkenyl, C 2 -C 6 -alkynyl, hydroxyl, C 1 -C 6 -alkoxy, C 3 -C 6 -alkenyloxy, C 3 -C 6 -alkynyloxy, amino, C 1 -C 6 -alkylamino, (di-(C 1 -C 6 )-alkyl)amino, C 1 -C 6 -alkoxyamino, C 1 -C 6 -alkylsulfonylamino, C 1 -C 6 -alkylaminosulfonylamino, (di-(C 1 -C 6 )-alkylamino)sulfonylamino, C 3 -C 6 -alkenylamino, C 3 -C 6 -alkynylamino, N—(C 2 -C 6 -alkenyl)-N—(C 1 -C 6 -alkyl)-amino, N—(C 2 -C 6 -alkynyl)-N—(C 1 -C 6 -alkyl)-amino, N—(C 1 -C 6 -alkoxy)-N—(C 1 -C 6 -alkyl)-amino, N—(C 2 -C 6 -alkenyl)-N—(C 1 -C 6 -alkoxy)-amino, N—(C 2 -C 6 -alkynyl)-N—(C 1 -C 6 -alkoxy)-amino, phenyl, phenoxy or wherein the alkyl moieties in the radicals listed under R 12  may be partially or fully halogenated and the phenyl moieties in the radicals listed under R 12  may carry 1, 2, 3 or 4 substituents R 12a  selected from the group consisting of halogen, CN, NO 2 , C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy and C 1 -C 4 -haloalkoxy; 
         R 2  is hydrogen, halogen, nitro, cyano, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 2 -C 4 -alkenyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, benzyl or a group S(O) n R 21  in which R 21  is C 1 -C 4 -alkyl or C 1 -C 4 -haloalkyl and n is 0, 1 or 2; 
         R 3  is hydrogen or halogen; 
         R 4  is C 1 -C 4 -alkyl, C 3 -C 4 -alkenyl or C 3 -C 4 -alkynyl; 
         R 5  is hydrogen, C 1 -C 4 -alkyl, C 3 -C 4 -alkenyl, C 3 -C 4 -alkynyl or a group C(═O)R 51  in which R 51  is hydrogen, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy or C 1 -C 4 -haloalkoxy; 
         R 6  is C 1 -C 4 -alkyl, C 1 -C 4 -hydroxyalkyl or C 1 -C 4 -haloalkyl; 
         R 7 , R 8  independently of one another are hydrogen, OH, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkyloxy, C 1 -C 4 -alkyl or C 1 -C 4 -haloalkyl; 
         R 9 , R 10  independently of one another are selected from the group consisting of hydrogen, halogen, CN, NO 2 , C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 2 -C 4 -alkenyl, C 1 -C 4 -alkoxy and C 1 -C 4 -haloalkoxy; and 
         R 11  is hydrogen or C 1 -C 4 -alkyl; 
         or an agriculturally useful salt of this compound. 
       
     
     
         18 . The piperazine compound according to  claim 17  in which R 1  is cyano, nitro or a 5- or 6-membered heteroaromatic radical which has either 1, 2 or 3 nitrogen atoms or 1 oxygen or 1 sulfur atom and, if appropriate, 1 or 2 nitrogen atoms as ring members and which is unsubstituted or may have 1 or 2 substituents selected from R 1a . 
     
     
         19 . The piperazine compound according to  claim 17  in which R 1  is halogen. 
     
     
         20 . The piperazine compound according to  claim 17  in which R 4  is 
     
     
         21 . The piperazine compound according to  claim 17  in which R 5  is hydrogen, methyl or ethyl. 
     
     
         22 . The piperazine compound according to  claim 17  in which R 5  is C(═O)R 51  in which R 51  is hydrogen, C 1 -C 4 -alkyl or C 1 -C 4 -haloalkyl. 
     
     
         23 . The piperazine compound according to  claim 17  in which R 6  is methyl or ethyl. 
     
     
         24 . The piperazine compound according to  claim 17  in which R 7  and R 8  are hydrogen. 
     
     
         25 . The piperazine compound according to  claim 17  in which R 10  is hydrogen. 
     
     
         26 . The piperazine compound according to  claim 17  in which R 11  is hydrogen. 
     
     
         27 . The piperazine compound according to  claim 17  of the general formula Ia in which R 1 , R 2 , R 3 , R 4 , R 5 , R 6  and R 9  have one of the meanings given in  claim 17 : 
       
         
           
           
               
               
           
         
         or an agriculturally useful salt of this compound. 
       
     
     
         28 . The piperazine compound according to  claim 27  in which
 R 1  is cyano or nitro;   R 2  is hydrogen, fluorine, chlorine, C 1 -C 2 -alkyl, ethenyl or C 1 -C 2 -alkoxy;   R 3  is fluorine or hydrogen;   R 3  is methyl;   R 5  is hydrogen, methyl or ethyl;   R 6  is methyl or ethyl; and   R 9  is hydrogen or halogen.   
     
     
         29 . The piperazine compound according to  claim 17 , selected from the group consisting of:
 2-[5-benzyl-1,4,5-trimethyl-3,6-dioxopiperazin-2-ylmethyl]benzonitrile,   2-[5-benzyl-1,4,5-trimethyl-3,6-dioxopiperazin-2-ylmethyl]-3-fluorobenzonitrile,   2-[5-benzyl-1,4,5-trimethyl-3,6-dioxopiperazin-2-ylmethyl]-3-methoxybenzonitrile,   2-[5-benzyl-1,4,5-trimethyl-3,6-dioxopiperazin-2-ylmethyl]-3,4-difluorobenzonitrile,   2-[5-benzyl-1,4,5-trimethyl-3,6-dioxopiperazin-2-ylmethyl]-3-methylbenzonitrile,   2-[5-benzyl-1,4,5-trimethyl-3,6-dioxopiperazin-2-ylmethyl]-3-ethenylbenzonitrile,   2-[5-benzyl-1,5-dimethyl-3,6-dioxopiperazin-2-ylmethyl]benzonitrile,   2-[5-benzyl-1,5-dimethyl-3,6-dioxopiperazin-2-ylmethyl]-3-fluorobenzonitrile,   2-[5-benzyl-1,5-dimethyl-3,6-dioxopiperazin-2-ylmethyl]-3-methoxybenzonitrile,   2-[5-benzyl-1,5-dimethyl-3,6-dioxopiperazin-2-ylmethyl]-3,4-difluorobenzonitrile,   2-[5-benzyl-1,5-dimethyl-3,6-dioxopiperazin-2-ylmethyl]-3-methylbenzonitrile,   2-[5-benzyl-1,5-dimethyl-3,6-dioxopiperazin-2-ylmethyl]-3-ethenylbenzonitrile,   2-[5-benzyl-5-ethyl-1,4-dimethyl-3,6-dioxopiperazin-2-ylmethyl]benzonitrile,   2-[5-benzyl-5-ethyl-1,4-dimethyl-3,6-dioxopiperazin-2-ylmethyl]-3-fluorobenzonitrile,   2-[5-benzyl-5-ethyl-1,4-dimethyl-3,6-dioxopiperazin-2-ylmethyl]-3-methoxybenzonitrile,   2-[5-benzyl-5-ethyl-1,4-dimethyl-3,6-dioxopiperazin-2-ylmethyl]-3,4-difluorobenzonitrile,   2-[5-benzyl-5-ethyl-1,4-dimethyl-3,6-dioxopiperazin-2-ylmethyl]-3-methylbenzonitrile,   2-[5-benzyl-5-ethyl-1,4-dimethyl-3,6-dioxopiperazin-2-ylmethyl]-3-ethenylbenzonitrile,   2-[5-benzyl-5-ethyl-1-methyl-3,6-dioxopiperazin-2-ylmethyl]benzonitrile,   2-[5-benzyl-5-ethyl-1-methyl-3,6-dioxopiperazin-2-ylmethyl]-3-fluorobenzonitrile,   2-[5-benzyl-5-ethyl-1-methyl-3,6-dioxopiperazin-2-ylmethyl]-3-methoxybenzonitrile,   2-[5-benzyl-5-ethyl-1-methyl-3,6-dioxopiperazin-2-ylmethyl]-3,4-difluorobenzonitrile,   2-[5-benzyl-5-ethyl-1-methyl-3,6-dioxopiperazin-2-ylmethyl]-3-methylbenzonitrile,   2-[5-benzyl-5-ethyl-1-methyl-3,6-dioxopiperazin-2-ylmethyl]-3-ethenylbenzonitrile,   2-[5-(4-fluorobenzyl)-1,4,5-trimethyl-3,6-dioxopiperazin-2-ylmethyl]benzonitrile,   2-[5-(4-fluorobenzyl)-1,4,5-trimethyl-3,6-dioxopiperazin-2-ylmethyl]-3-fluorobenzonitrile,   2-[5-(4-fluorobenzyl)-1,4,5-trimethyl-3,6-dioxopiperazin-2-ylmethyl]-3-methoxybenzonitrile,   2-[5-(4-fluorobenzyl)-1,4,5-trimethyl-3,6-dioxopiperazin-2-ylmethyl]-3,4-difluorobenzonitrile,   2-[5-(4-fluorobenzyl)-1,4,5-trimethyl-3,6-dioxopiperazin-2-ylmethyl]-3-methylbenzonitrile,   2-[5-(4-fluorobenzyl)-1,4,5-trimethyl-3,6-dioxopiperazin-2-ylmethyl]-3-ethenylbenzonitrile,   2-[5-(4-fluorobenzyl)-1,5-dimethyl-3,6-dioxopiperazin-2-ylmethyl]benzonitrile,   2-[5-(4-fluorobenzyl)-1,5-dimethyl-3,6-dioxopiperazin-2-ylmethyl]-3-fluorobenzonitrile,   2-[5-(4-fluorobenzyl)-1,5-dimethyl-3,6-dioxopiperazin-2-ylmethyl]-3-methoxybenzonitrile,   2-[5-(4-fluorobenzyl)-1,5-dimethyl-3,6-dioxopiperazin-2-ylmethyl]-3,4-difluorobenzonitrile,   2-[5-(4-fluorobenzyl)-1,5-dimethyl-3,6-dioxopiperazin-2-ylmethyl]-3-methylbenzonitrile,   2-[5-(4-fluorobenzyl)-1,5-dimethyl-3,6-dioxopiperazin-2-ylmethyl]-3-ethenylbenzonitrile,   2-[5-(4-fluorobenzyl)-5-ethyl-1,4-dimethyl-3,6-dioxopiperazin-2-ylmethyl]-benzonitrile,   2-[5-(4-fluorobenzyl)-5-ethyl-1,4-dimethyl-3,6-dioxopiperazin-2-ylmethyl]-3-fluorobenzonitrile,   2-[5-(4-fluorobenzyl)-5-ethyl-1,4-dimethyl-3,6-dioxopiperazin-2-ylmethyl]-3-methoxybenzonitrile,   2-[5-(4-fluorobenzyl)-5-ethyl-1,4-dimethyl-3,6-dioxopiperazin-2-ylmethyl]-3,4-difluorobenzonitrile,   2-[5-(4-fluorobenzyl)-5-ethyl-1,4-dimethyl-3,6-dioxopiperazin-2-ylmethyl]-3-methylbenzonitrile,   2-[5-(4-fluorobenzyl)-5-ethyl-1,4-dimethyl-3,6-dioxopiperazin-2-ylmethyl]-3-ethenylbenzonitrile,   2-[5-(4-fluorobenzyl)-5-ethyl-1-methyl-3,6-dioxopiperazin-2-ylmethyl]benzonitrile,   2-[5-(4-fluorobenzyl)-5-ethyl-1-methyl-3,6-dioxopiperazin-2-ylmethyl]-3-fluorobenzonitrile,   2-[5-(4-fluorobenzyl)-5-ethyl-1-methyl-3,6-dioxopiperazin-2-ylmethyl]-3-methoxybenzonitrile,   2-[5-(4-fluorobenzyl)-5-ethyl-1-methyl-3,6-dioxopiperazin-2-ylmethyl]-3,4-difluorobenzonitrile,   2-[5-(4-fluorobenzyl)-5-ethyl-1-methyl-3,6-dioxopiperazin-2-ylmethyl]-3-methylbenzonitrile,   2-[5-(4-fluorobenzyl)-5-ethyl-1-methyl-3,6-dioxopiperazin-2-ylmethyl]-3-ethenylbenzonitrile,   3-benzyl-6-(2-nitrobenzyl)-1,3,4-trimethylpiperazine-2,5-dione,   3-benzyl-6-(2-fluoro-6-nitrobenzyl)-1,3,4-trimethylpiperazine-2,5-dione,   3-benzyl-6-(2,3-difluoro-6-nitrobenzyl)-1,3,4-trimethylpiperazine-2,5-dione,   3-benzyl-6-(2-methoxy-6-nitrobenzyl)-1,3,4-trimethylpiperazine-2,5-dione,   3-benzyl-6-(2-methyl-6-nitrobenzyl)-1,3,4-trimethylpiperazine-2,5-dione,   3-benzyl-6-(2-ethenyl-6-nitrobenzyl)-1,3,4-trimethylpiperazine-2,5-dione,   3-benzyl-6-(2-nitrobenzyl)-1,3-dimethylpiperazine-2,5-dione,   3-benzyl-6-(2-fluoro-6-nitrobenzyl)-1,3-dimethylpiperazine-2,5-dione,   3-benzyl-6-(2,3-difluoro-6-nitrobenzyl)-1,3-dimethylpiperazine-2,5-dione,   3-benzyl-6-(2-methoxy-6-nitrobenzyl)-1,3-dimethylpiperazine-2,5-dione,   3-benzyl-6-(2-methyl-6-nitrobenzyl)-1,3-dimethylpiperazine-2,5-dione,   3-benzyl-6-(2-ethenyl-6-nitrobenzyl)-1,3-dimethylpiperazine-2,5-dione,   3-benzyl-6-(2-nitrobenzyl)-3-ethyl-1,4-dimethylpiperazine-2,5-dione,   3-benzyl-6-(2-fluoro-6-nitrobenzyl)-3-ethyl-1,4-dimethylpiperazine-2,5-dione,   3-benzyl-6-(2,3-difluoro-6-nitrobenzyl)-3-ethyl-1,4-dimethylpiperazine-2,5-dione,   3-benzyl-6-(2-methoxy-6-nitrobenzyl)-3-ethyl-1,4-dimethylpiperazine-2,5-dione,   3-benzyl-6-(2-methyl-6-nitrobenzyl)-3-ethyl-1,4-dimethylpiperazine-2,5-dione,   3-benzyl-6-(2-ethenyl-6-nitrobenzyl)-3-ethyl-1,4-dimethylpiperazine-2,5-dione,   3-benzyl-6-(2-nitrobenzyl)-3-ethyl-1-methylpiperazine-2,5-dione,   3-benzyl-6-(2-fluoro-6-nitrobenzyl)-3-ethyl-1-methylpiperazine-2,5-dione,   3-benzyl-6-(2,3-difluoro-6-nitrobenzyl)-3-ethyl-1-methylpiperazine-2,5-dione,   3-benzyl-6-(2-methoxy-6-nitrobenzyl)-3-ethyl-1-methylpiperazine-2,5-dione,   3-benzyl-6-(2-methyl-6-nitrobenzyl)-3-ethyl-1-methylpiperazine-2,5-dione,   3-benzyl-6-(2-ethenyl-6-nitrobenzyl)-3-ethyl-1-methylpiperazine-2,5-dione,   3-(4-fluorobenzyl)-6-(2-nitrobenzyl)-1,3,4-trimethylpiperazine-2,5-dione,   3-(4-fluorobenzyl)-6-(2-fluoro-6-nitrobenzyl)-1,3,4-trimethylpiperazine-2,5-dione,   3-(4-fluorobenzyl)-6-(2,3-difluoro-6-nitrobenzyl)-1,3,4-trimethylpiperazine-2,5-dione,   3-(4-fluorobenzyl)-6-(2-methoxy-6-nitrobenzyl)-1,3,4-trimethylpiperazine-2,5-dione,   3-(4-fluorobenzyl)-6-(2-methyl-6-nitrobenzyl)-1,3,4-trimethylpiperazine-2,5-dione,   3-(4-fluorobenzyl)-6-(2-ethenyl-6-nitrobenzyl)-1,3,4-trimethylpiperazine-2,5-dione,   3-(4-fluorobenzyl)-6-(2-nitrobenzyl)-1,3-dimethylpiperazine-2,5-dione,   3-(4-fluorobenzyl)-6-(2-fluoro-6-nitrobenzyl)-1,3-dimethylpiperazine-2,5-dione,   3-(4-fluorobenzyl)-6-(2,3-difluoro-6-nitrobenzyl)-1,3-dimethylpiperazine-2,5-dione,   3-(4-fluorobenzyl)-6-(2-methoxy-6-nitrobenzyl)-1,3-dimethylpiperazine-2,5-dione,   3-(4-fluorobenzyl)-6-(2-methyl-6-nitrobenzyl)-1,3-dimethylpiperazine-2,5-dione,   3-(4-fluorobenzyl)-6-(2-ethenyl-6-nitrobenzyl)-1,3-dimethylpiperazine-2,5-dione,   3-(4-fluorobenzyl)-6-(2-nitrobenzyl)-3-ethyl-1,4-dimethylpiperazine-2,5-dione,   3-(4-fluorobenzyl)-6-(2-fluoro-6-nitrobenzyl)-3-ethyl-1,4-dimethylpiperazine-2,5-dione,   3-(4-fluorobenzyl)-6-(2,3-difluoro-6-nitrobenzyl)-3-ethyl-1,4-dimethylpiperazine-2,5-dione,   3-(4-fluorobenzyl)-6-(2-methoxy-6-nitrobenzyl)-3-ethyl-1,4-dimethylpiperazine-2,5-dione,   3-(4-fluorobenzyl)-6-(2-methyl-6-nitrobenzyl)-3-ethyl-1,4-dimethylpiperazine-2,5-dione,   3-(4-fluorobenzyl)-6-(2-ethenyl-6-nitrobenzyl)-3-ethyl-1,4-dimethylpiperazine-2,5-dione,   3-(4-fluorobenzyl)-6-(2-nitrobenzyl)-3-ethyl-1-methylpiperazine-2,5-dione,   3-(4-fluorobenzyl)-6-(2-fluoro-6-nitrobenzyl)-3-ethyl-1-methylpiperazine-2,5-dione,   3-(4-fluorobenzyl)-6-(2,3-difluoro-6-nitrobenzyl)-3-ethyl-1-methylpiperazine-2,5-dione,   3-(4-fluorobenzyl)-6-(2-methoxy-6-nitrobenzyl)-3-ethyl-1-methylpiperazine-2,5-dione,   3-(4-fluorobenzyl)-6-(2-methyl-6-nitrobenzyl)-3-ethyl-1-methylpiperazine-2,5-dione, and   3-(4-fluorobenzyl)-6-(2-ethenyl-6-nitrobenzyl)-3-ethyl-1-methylpiperazine-2,5-dione.   
     
     
         30 . A composition comprising a herbicidally effective amount of at least one piperazine compound of the formula I, or an agriculturally useful salt thereof, according to  claim 17  and auxiliaries customary for formulating crop protection agents. 
     
     
         31 . The composition of  claim 30 , wherein the compound has the general formula Ia: 
       
         
           
           
               
               
           
         
         or an agriculturally useful salt thereof. 
       
     
     
         32 . A method for controlling unwanted vegetation wherein a herbicidally effective amount of at least one piperazine compound of the formula I or Ia or an agriculturally useful salt of I according  claim 17  is allowed to act on plants, their seed and/or their habitat. 
     
     
         33 . The method of  claim 32  wherein the compound has the general formula Ia: 
       
         
           
           
               
               
           
         
         or an agriculturally useful salt thereof. 
       
     
     
         34 . The method of  claim 32 , wherein the compound is selected from the group consisting of:
 2-[5-benzyl-1,4,5-trimethyl-3,6-dioxopiperazin-2-ylmethyl]benzonitrile,   2-[5-benzyl-1,4,5-trimethyl-3,6-dioxopiperazin-2-ylmethyl]-3-fluorobenzonitrile,   2-[5-benzyl-1,4,5-trimethyl-3,6-dioxopiperazin-2-ylmethyl]-3-methoxybenzonitrile,   2-[5-benzyl-1,4,5-trimethyl-3,6-dioxopiperazin-2-ylmethyl]-3,4-difluorobenzonitrile,   2-[5-benzyl-1,4,5-trimethyl-3,6-dioxopiperazin-2-ylmethyl]-3-methylbenzonitrile,   2-[5-benzyl-1,4,5-trimethyl-3,6-dioxopiperazin-2-ylmethyl]-3-ethenylbenzonitrile,   2-[5-benzyl-1,5-dimethyl-3,6-dioxopiperazin-2-ylmethyl]benzonitrile,   2-[5-benzyl-1,5-dimethyl-3,6-dioxopiperazin-2-ylmethyl]-3-fluorobenzonitrile,   2-[5-benzyl-1,5-dimethyl-3,6-dioxopiperazin-2-ylmethyl]-3-methoxybenzonitrile,   2-[5-benzyl-1,5-dimethyl-3,6-dioxopiperazin-2-ylmethyl]-3,4-difluorobenzonitrile,   2-[5-benzyl-1,5-dimethyl-3,6-dioxopiperazin-2-ylmethyl]-3-methylbenzonitrile,   2-[5-benzyl-1,5-dimethyl-3,6-dioxopiperazin-2-ylmethyl]-3-ethenylbenzonitrile,   2-[5-benzyl-5-ethyl-1,4-dimethyl-3,6-dioxopiperazin-2-ylmethyl]benzonitrile,   2-[5-benzyl-5-ethyl-1,4-dimethyl-3,6-dioxopiperazin-2-ylmethyl]-3-fluorobenzonitrile,   2-[5-benzyl-5-ethyl-1,4-dimethyl-3,6-dioxopiperazin-2-ylmethyl]-3-methoxybenzonitrile,   2-[5-benzyl-5-ethyl-1,4-dimethyl-3,6-dioxopiperazin-2-ylmethyl]-3,4-difluorobenzonitrile,   2-[5-benzyl-5-ethyl-1,4-dimethyl-3,6-dioxopiperazin-2-ylmethyl]-3-methylbenzonitrile,   2-[5-benzyl-5-ethyl-1,4-dimethyl-3,6-dioxopiperazin-2-ylmethyl]-3-ethenylbenzonitrile,   2-[5-benzyl-5-ethyl-1-methyl-3,6-dioxopiperazin-2-ylmethyl]benzonitrile,   2-[5-benzyl-5-ethyl-1-methyl-3,6-dioxopiperazin-2-ylmethyl]-3-fluorobenzonitrile,   2-[5-benzyl-5-ethyl-1-methyl-3,6-dioxopiperazin-2-ylmethyl]-3-methoxybenzonitrile,   2-[5-benzyl-5-ethyl-1-methyl-3,6-dioxopiperazin-2-ylmethyl]-3,4-difluorobenzonitrile,   2-[5-benzyl-5-ethyl-1-methyl-3,6-dioxopiperazin-2-ylmethyl]-3-methylbenzonitrile,   2-[5-benzyl-5-ethyl-1-methyl-3,6-dioxopiperazin-2-ylmethyl]-3-ethenylbenzonitrile,   2-[5-(4-fluorobenzyl)-1,4,5-trimethyl-3,6-dioxopiperazin-2-ylmethyl]benzonitrile,   2-[5-(4-fluorobenzyl)-1,4,5-trimethyl-3,6-dioxopiperazin-2-ylmethyl]-3-fluorobenzonitrile,   2-[5-(4-fluorobenzyl)-1,4,5-trimethyl-3,6-dioxopiperazin-2-ylmethyl]-3-methoxybenzonitrile,   2-[5-(4-fluorobenzyl)-1,4,5-trimethyl-3,6-dioxopiperazin-2-ylmethyl]-3,4-difluorobenzonitrile,   2-[5-(4-fluorobenzyl)-1,4,5-trimethyl-3,6-dioxopiperazin-2-ylmethyl]-3-methylbenzonitrile,   2-[5-(4-fluorobenzyl)-1,4,5-trimethyl-3,6-dioxopiperazin-2-ylmethyl]-3-ethenylbenzonitrile,   2-[5-(4-fluorobenzyl)-1,5-dimethyl-3,6-dioxopiperazin-2-ylmethyl]benzonitrile,   2-[5-(4-fluorobenzyl)-1,5-dimethyl-3,6-dioxopiperazin-2-ylmethyl]-3-fluorobenzonitrile,   2-[5-(4-fluorobenzyl)-1,5-dimethyl-3,6-dioxopiperazin-2-ylmethyl]-3-methoxybenzonitrile,   2-[5-(4-fluorobenzyl)-1,5-dimethyl-3,6-dioxopiperazin-2-ylmethyl]-3,4-difluorobenzonitrile,   2-[5-(4-fluorobenzyl)-1,5-dimethyl-3,6-dioxopiperazin-2-ylmethyl]-3-methylbenzonitrile,   2-[5-(4-fluorobenzyl)-1,5-dimethyl-3,6-dioxopiperazin-2-ylmethyl]-3-ethenylbenzonitrile,   2-[5-(4-fluorobenzyl)-5-ethyl-1,4-dimethyl-3,6-dioxopiperazin-2-ylmethyl]-benzonitrile,   2-[5-(4-fluorobenzyl)-5-ethyl-1,4-dimethyl-3,6-dioxopiperazin-2-ylmethyl]-3-fluorobenzonitrile,   2-[5-(4-fluorobenzyl)-5-ethyl-1,4-dimethyl-3,6-dioxopiperazin-2-ylmethyl]-3-methoxybenzonitrile,   2-[5-(4-fluorobenzyl)-5-ethyl-1,4-dimethyl-3,6-dioxopiperazin-2-ylmethyl]-3,4-difluorobenzonitrile,   2-[5-(4-fluorobenzyl)-5-ethyl-1,4-dimethyl-3,6-dioxopiperazin-2-ylmethyl]-3-methylbenzonitrile,   2-[5-(4-fluorobenzyl)-5-ethyl-1,4-dimethyl-3,6-dioxopiperazin-2-ylmethyl]-3-ethenylbenzonitrile,   2-[5-(4-fluorobenzyl)-5-ethyl-1-methyl-3,6-dioxopiperazin-2-ylmethyl]benzonitrile,   2-[5-(4-fluorobenzyl)-5-ethyl-1-methyl-3,6-dioxopiperazin-2-ylmethyl]-3-fluorobenzonitrile,   2-[5-(4-fluorobenzyl)-5-ethyl-1-methyl-3,6-dioxopiperazin-2-ylmethyl]-3-methoxybenzonitrile,   2-[5-(4-fluorobenzyl)-5-ethyl-1-methyl-3,6-dioxopiperazin-2-ylmethyl]-3,4-difluorobenzonitrile,   2-[5-(4-fluorobenzyl)-5-ethyl-1-methyl-3,6-dioxopiperazin-2-ylmethyl]-3-methylbenzonitrile,   2-[5-(4-fluorobenzyl)-5-ethyl-1-methyl-3,6-dioxopiperazin-2-ylmethyl]-3-ethenylbenzonitrile,   3-benzyl-6-(2-nitrobenzyl)-1,3,4-trimethylpiperazine-2,5-dione,   3-benzyl-6-(2-fluoro-6-nitrobenzyl)-1,3,4-trimethylpiperazine-2,5-dione,   3-benzyl-6-(2,3-difluoro-6-nitrobenzyl)-1,3,4-trimethylpiperazine-2,5-dione,   3-benzyl-6-(2-methoxy-6-nitrobenzyl)-1,3,4-trimethylpiperazine-2,5-dione,   3-benzyl-6-(2-methyl-6-nitrobenzyl)-1,3,4-trimethylpiperazine-2,5-dione,   3-benzyl-6-(2-ethenyl-6-nitrobenzyl)-1,3,4-trimethylpiperazine-2,5-dione,   3-benzyl-6-(2-nitrobenzyl)-1,3-dimethylpiperazine-2,5-dione,   3-benzyl-6-(2-fluoro-6-nitrobenzyl)-1,3-dimethylpiperazine-2,5-dione,   3-benzyl-6-(2,3-difluoro-6-nitrobenzyl)-1,3-dimethylpiperazine-2,5-dione,   3-benzyl-6-(2-methoxy-6-nitrobenzyl)-1,3-dimethylpiperazine-2,5-dione,   3-benzyl-6-(2-methyl-6-nitrobenzyl)-1,3-dimethylpiperazine-2,5-dione,   3-benzyl-6-(2-ethenyl-6-nitrobenzyl)-1,3-dimethylpiperazine-2,5-dione,   3-benzyl-6-(2-nitrobenzyl)-3-ethyl-1,4-dimethylpiperazine-2,5-dione,   3-benzyl-6-(2-fluoro-6-nitrobenzyl)-3-ethyl-1,4-dimethylpiperazine-2,5-dione,   3-benzyl-6-(2,3-difluoro-6-nitrobenzyl)-3-ethyl-1,4-dimethylpiperazine-2,5-dione,   3-benzyl-6-(2-methoxy-6-nitrobenzyl)-3-ethyl-1,4-dimethylpiperazine-2,5-dione,   3-benzyl-6-(2-methyl-6-nitrobenzyl)-3-ethyl-1,4-dimethylpiperazine-2,5-dione,   3-benzyl-6-(2-ethenyl-6-nitrobenzyl)-3-ethyl-1,4-dimethylpiperazine-2,5-dione,   3-benzyl-6-(2-nitrobenzyl)-3-ethyl-1-methylpiperazine-2,5-dione,   3-benzyl-6-(2-fluoro-6-nitrobenzyl)-3-ethyl-1-methylpiperazine-2,5-dione,   3-benzyl-6-(2,3-difluoro-6-nitrobenzyl)-3-ethyl-1-methylpiperazine-2,5-dione,   3-benzyl-6-(2-methoxy-6-nitrobenzyl)-3-ethyl-1-methylpiperazine-2,5-dione,   3-benzyl-6-(2-methyl-6-nitrobenzyl)-3-ethyl-1-methylpiperazine-2,5-dione,   3-benzyl-6-(2-ethenyl-6-nitrobenzyl)-3-ethyl-1-methylpiperazine-2,5-dione,   3-(4-fluorobenzyl)-6-(2-nitrobenzyl)-1,3,4-trimethylpiperazine-2,5-dione,   3-(4-fluorobenzyl)-6-(2-fluoro-6-nitrobenzyl)-1,3,4-trimethylpiperazine-2,5-dione,   3-(4-fluorobenzyl)-6-(2,3-difluoro-6-nitrobenzyl)-1,3,4-trimethylpiperazine-2,5-dione,   3-(4-fluorobenzyl)-6-(2-methoxy-6-nitrobenzyl)-1,3,4-trimethylpiperazine-2,5-dione,   3-(4-fluorobenzyl)-6-(2-methyl-6-nitrobenzyl)-1,3,4-trimethylpiperazine-2,5-dione,   3-(4-fluorobenzyl)-6-(2-ethenyl-6-nitrobenzyl)-1,3,4-trimethylpiperazine-2,5-dione,   3-(4-fluorobenzyl)-6-(2-nitrobenzyl)-1,3-dimethylpiperazine-2,5-dione,   3-(4-fluorobenzyl)-6-(2-fluoro-6-nitrobenzyl)-1,3-dimethylpiperazine-2,5-dione,   3-(4-fluorobenzyl)-6-(2,3-difluoro-6-nitrobenzyl)-1,3-dimethylpiperazine-2,5-dione,   3-(4-fluorobenzyl)-6-(2-methoxy-6-nitrobenzyl)-1,3-dimethylpiperazine-2,5-dione,   3-(4-fluorobenzyl)-6-(2-methyl-6-nitrobenzyl)-1,3-dimethylpiperazine-2,5-dione,   3-(4-fluorobenzyl)-6-(2-ethenyl-6-nitrobenzyl)-1,3-dimethylpiperazine-2,5-dione,   3-(4-fluorobenzyl)-6-(2-nitrobenzyl)-3-ethyl-1,4-dimethylpiperazine-2,5-dione,   3-(4-fluorobenzyl)-6-(2-fluoro-6-nitrobenzyl)-3-ethyl-1,4-dimethylpiperazine-2,5-dione,   3-(4-fluorobenzyl)-6-(2,3-difluoro-6-nitrobenzyl)-3-ethyl-1,4-dimethylpiperazine-2,5-dione,   3-(4-fluorobenzyl)-6-(2-methoxy-6-nitrobenzyl)-3-ethyl-1,4-dimethylpiperazine-2,5-dione,   3-(4-fluorobenzyl)-6-(2-methyl-6-nitrobenzyl)-3-ethyl-1,4-dimethylpiperazine-2,5-dione,   3-(4-fluorobenzyl)-6-(2-ethenyl-6-nitrobenzyl)-3-ethyl-1,4-dimethylpiperazine-2,5-dione,   3-(4-fluorobenzyl)-6-(2-nitrobenzyl)-3-ethyl-1-methylpiperazine-2,5-dione,   3-(4-fluorobenzyl)-6-(2-fluoro-6-nitrobenzyl)-3-ethyl-1-methylpiperazine-2,5-dione,   3-(4-fluorobenzyl)-6-(2,3-difluoro-6-nitrobenzyl)-3-ethyl-1-methylpiperazine-2,5-dione,   3-(4-fluorobenzyl)-6-(2-methoxy-6-nitrobenzyl)-3-ethyl-1-methylpiperazine-2,5-dione,   3-(4-fluorobenzyl)-6-(2-methyl-6-nitrobenzyl)-3-ethyl-1-methylpiperazine-2,5-dione, and   3-(4-fluorobenzyl)-6-(2-ethenyl-6-nitrobenzyl)-3-ethyl-1-methylpiperazine-2,5-dione.   
     
     
         35 . The method of  claim 32  in which R 1  is cyano, nitro or a 5- or 6-membered heteroaromatic radical which has either 1, 2 or 3 nitrogen atoms or 1 oxygen or 1 sulfur atom and, if appropriate, 1 or 2 nitrogen atoms as ring members and which is unsubstituted or may have 1 or 2 substituents selected from R 1a . 
     
     
         36 . The method of  claim 32  in which R 1  is halogen.

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